Why Some Men Still Dress Like They’re 16

Why do some men never outgrow band T-shirts and jeans?

Aymann Ismail: Like me, John grew up skating, collecting band T-shirts, and making fun of the way that other guys put actual thought into their outfits. I considered myself someone who focused on real things, like doing good in school or being able to jump high enough to dunk a basketball. Putting that much thought into how I looked? No way, that’s desperate.

Yo, I can so still relate. Almost all of the T-shirts that I have I’ve pretty much gotten for free. They have a “you donated blood” logo on them, or—Bank of America T-shirts. I also, very similarly, feel a little guilty for that. So I want to know why you feel like that. What part of you is trying to convince you that you need to change your look?

That hits home for me—not wanting to take too much of a risk because I have no real way of knowing how I look in these clothes. Like I look in the mirror and think to myself,. And if I ask anyone that I know, “Hey, what do you think of this?” a part of me will kind of feel corny. Like I’m trying too hard.Now that I’m an adult with a “grown-up job,” I’m trying to also buy clothes that aren’t as disposable.

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